Methanol → HCID 58763421, compound

HRID 858279Notes

Reaction equation

HRID 858279 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]([OH:15])=[O:14].OS(O)(=O)=O.[CH3:21]O>>[OH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]([O:15][CH3:21])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 166410173-(2-Hydroxyethyl)-1H-indole-2-carboxylic acid

Product 1

HCID 58763421HCID 58763421, compound

Procedure

To a solution of 3-(2-hydroxyethyl)-1H-indole-2-carboxylic acid (5.589 g, 26.1 mmol) in methanol (75 mL) was added concentrated H2SO4 (3 mL), and the mixture was refluxed overnight. The solvent was removed under a reduced pressure and the residual oil was dissolved in EtOAc. The organic solution was washed with a saturated aqueous NaHCO3 solution, dried over Na2SO4, and concentrated to give 5.670 g of methyl 3-(2-hydroxyethyl)-1H-indole-2-carboxylate as an oil. This material was used for the next reaction without further purification: 1H NMR (CDCl3) δ 2.21 (brs, 1H), 3.40 (t, J=6.5 Hz, 2H), 3.88 (s, 3H), 3.94 (t, J=6.5 Hz, 2H), 7.14 (ddd, J=1.7, 6.3, and 8.1 Hz, 1H), 7.2–7.4 (m, 2H), 7.70 (d, J=8.1 Hz, 1H), 9.07 (brs, 1H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was removed under a reduced pressure
  3. dissolutionthe residual oil was dissolved in EtOAc
  4. washThe organic solution was washed with a saturated aqueous NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b5d3dd8a8c8e4106a0cbc6d0f38fc14a
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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